Only once in my life did a girl fly in to meet me, it didn’t go well. She didn’t know anyone in NY and didn’t really have anything to do, besides see me. The biggest mistake of the whole venture was that we spoke on the phone for a longer time than should’ve been. Talking on the phone for longer than a couple weeks and then being let down in person is the plague of being a GU. (frum dating vernacular for geographically undesirable aka out of town) Being in shidduchim is hard enough as it is, throw in a flight, being in a strange place, and having to risk spending a weekend with someone who instantly turns you off is like being forced to go on a second dates when you knew it wasn’t going to work out.
For most folks living out of town, their idea of dating involves a weekend in New York and trying to fit in as many Saw You At Sinai girls as possible. I have one friend who would try to go out with 6-10 girls over a weekend and by the time he was done he had no idea which one was which. I’m not sure if girls do shidduch marathons like guys do, but I’m sure there are girls going out with several guys in a day just to make their travel time worthwhile. What changes is when the person is traveling to a place just to see one person. For instance, if someone decides to travel to the Bay Area to go out with one girl, there is hardly any chance that he will be dating anyone else here. What happens if that person comes for 3 days and on the first date it doesn’t work out. Chances are, if he/she’s a frummy type, they’re staying at some friends or rabbis of the person they came to date, it must get real awkward when the person decides that after one day they want no more. More realistic are the people who travel for dating with adventure in mind, they may not feel their date was marriageable, but that doesn’t mean they can’t hang out and enjoy each others’ company…unless that’s not tznius.
The best way to date GU’s is to talk on the phone minimally and maybe have a skype date. Skype is blurry and doesn’t make for good yichud action, but it does show you if the chemistry’s good. Talking on the phone for 6 months and then meeting can always be such a big let down and then you feel like you wasted too much time.
Basically when someone comes out to date you, make sure they have something to do besides hang out with you. You don’t want to be stuck with someone who repulses you.